Tetrazine

    Tetrazine is an unstable compound that consists of a six-membered aromatic ring containing four nitrogen atoms with the molecular formula C₂H₂N₄. The name tetrazine is used in the nomenclature of derivatives of this compound. Three core-ring isomers exist: 1,2,3,4-tetrazines, 1,2,3,5-tetrazines and 1,2,4,5-tetrazines

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1,2,3,4-tetrazines

1,2,3,4-Tetrazines are often isolated fused to an aromatic ring system and are stablized as the dioxide derivatives.

1,2,4,5-tetrazine

1,2,4,5-Tetrazines are very well known and myriad 3,6-disubstituted 1,2,4,5-tetrazines are known ^[1]. These materials are of use in the area of energetic chemistry.

The compound 3,6-di-2-pyridyl-1,2,4,5-tetrazine ^[2] has two pyridine substituents and is of importance as a reagent in Diels-Alder reactions. It reacts with norbornadiene in a sequence of one DA reactions and two retro-DA reactions to cyclopentadiene and a pyridazine with exchange of an acetylene unit:

With norbornadiene fused to an arene the reaction stops at an intermediary stage ^[3]

See also

• 6-membered rings with three nitrogen atoms: triazines
• 6-membered rings with two nitrogen atoms: diazines
• Pyridine

References